Chiral counteranions in asymmetric transition-metal catalysis: Highly enantioselective Pd/Brønsted acid-catalyzed direct α-allylation of aldehydes

Journal of the American Chemical Society

Volumn 129, Issue 37, 2007, Pages 11336-11337

  Mukherjee, Santanu ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BRONSTED ACID; PALLADIUM; TRANSITION ELEMENT;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 35048885691     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074678r     Document Type: Article

References (42)

1. (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566-1568.
2. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356-5357.
3. For reviews see: (c) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999-1010.
4. (d) Connon, S. J. Angew. Chem., Int. Ed. 2006, 45, 3909-3912 and references therein.
5. List, B. Chem. Commun. 2006, 819-824 and references therein.
6. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193-4195.
7. For earlier attempts, see: Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373-382.
8. (a) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368-13369.
9. (b) Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498-7499.
10. For reviews see: (a) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395-422.
11. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
12. (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
13. Chiral phosphates have been used before in the Pd-catalyzed asymmetric hydrocarboxylation of olefins. See: Alper, H.; Hamel, N. J. Am. Chem. Soc. 1990, 112, 2803-2804.
14. For the application of chiral phosphoric acids in metal mediated asymmetric transformations see: (a) Lacasse, M.-C.; Poulard, C.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 12440-12441.
15. (b) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448-16449.
16. Also see: (c) Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165-4168.
17. For reviews see: (a) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-5367.
18. (b) Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473-1482.
19. (c) Trost, B. M.; Jiang, C. Synthesis 2006, 369-396.
20. For a direct intramolecular α-alkylation of aldehydes see: (a) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451.
21. For tin enolate-based approaches see: (b) Doyle, A. G.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 3701-3705 and the references therein.
22. For the α-allylation using phase transfer catalysts see: Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222-4266 and references therein.
23. For a nonasymmetric direct α-allylation of aldehydes see: Kimura, M.; Horino, Y.; Mukai, R.; Tanaka, S.; Tamara, Y. J. Am. Chem. Soc. 2001, 123, 10401-10402.
24. For reviews about allylic alkylation of ketone enolates see: (a) Tunge, J. A.; Burger, E. C. Eur. J. Org. Chem. 2005, 1715-1726.
25. (b) Braun, M.; Meier, T. Angew. Chem., Int. Ed. 2006, 45, 6952-6955.
26. (c) Braun, M.; Meier, T. Synlett 2006, 661-676.
27. For recent advances see: (d) Benenna, D. C.; Stolz, B. M. J. Am. Chem. Soc. 2004, 126, 15044-15045.
28. (e) Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 2846-2847.
29. (f) Graening, T.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 17192-17193.
30. (g) Belanger, E.; Cantin, K.; Messe, O.; Tremblay, M.; Paquin, J.-F. J. Am. Chem. Soc. 2007, 129, 1034-1035.
31. For a catalytic enantioselective allylic alkylation of enamines, see: (a) Weix, D. J.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7720-7721.
32. For auxiliary-based approaches see: (b) Hiroi, K.; Abe, J.; Suya, K.; Sato, S. Tetrahedron Lett. 1989, 30, 1543-1546.
33. (c) Hiroi, K.; Abe, J. Tetrahedron Lett. 1990, 31, 3623-3626.
34. (d) Hiroi, K.; Koyama, T.; Anzai, K. Chem. Lett. 1990, 235-238.
35. (e) Hiroi, K.; Abe, J.; Suya, K.; Sato, S.; Koyama, T. J. Org. Chem. 1994, 59, 203-213.
36. Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952-1956.
37. Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582-585.
38. (a) Murahashi, S.-I.; Makabe, Y. Tetrahedron Lett. 1985, 26, 5563-5566.
39. (b) Murahashi, S.-I.; Makabe, Y.; Kunita, K. J. Org. Chem. 1988, 53, 4489-4495.
40. 3) (3 mol %), and (R)-TRIP (1.5 mol %) were reacted at 40°C, full conversion to α-allylated aldehyde 2a in 89:11 er was obtained.
41. 4 rather than by acidic hydrolysis, the corresponding amine is obtained: (Chemical Equation Presented)
42. Reetz, M. T.; Westermann, J.; Kyung, S.-H. Chem. Ber. 1985, 118, 1050-1057.